4-Nitrobenzaldehyde → HCID 10661075, compound

HRID 350719Notes

Reaction equation

HRID 350719 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[PH2:12]([O:14][CH2:15][CH3:16])=[O:13].C(N(CC)CC)C.C([O:27][CH2:28][CH3:29])(=O)C>>[OH:9][CH:8]([P:12](=[O:13])([O:27][CH2:28][CH3:29])[O:14][CH2:15][CH3:16])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 178476775HCID 178476775, compound

Product 1

HCID 10661075HCID 10661075, compound

Procedure

To a mixture of 4-nitrobenzaldehyde (8.56 g) and ethyl hypophosphite (7.81 g) was gradually added triethylamine (1.5 mL). After stirring for 1 hr., the reaction mixture was diluted with ethyl acetate and washed successively with 1N hydrochloric acid and water. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, and diethyl α-hydroxy-4-nitrobenzylphosphonate was obtained as crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). Recrystallization from ethyl acetate-hexane gave yellow prism crystals (4.62 g, yield 28%). melting point: 94–95° C.

Workup

  1. washwashed successively with 1N hydrochloric acid and water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-44ecfd4c70d145ad967c24426bde536e
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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